The allure of Chicago, often affectionately dubbed the "Windy City," stems from its rich tapestry of experiences. It’s a city that proudly showcases its pioneering architectural achievements, tantalizes taste buds with a vibrant culinary scene, and keeps the laughter flowing with its renowned comedy clubs. Moreover, Chicago boasts world-class museums and a plethora of tourist attractions that cater to both first-time visitors and seasoned travelers. To help you navigate the abundance of choices and maximize your weekend getaway, we have curated an itinerary highlighting the must-visit spots that define the essence of Chicago. From exceptional dining experiences to exhilarating entertainment options, prepare for an unparalleled 48 hours in Chicago. This itinerary is designed to immerse you in the heart of the city, leaving you with memories that will last a lifetime.
Day 1: Morning
10:00 AM: Stroll Along the Chicago Riverwalk
One of the most captivating ways to immerse yourself in the vibrant atmosphere of the city is by taking a leisurely walk along the renowned Chicago Riverwalk. This 1.25-mile-long, meticulously maintained path offers a unique perspective on the city’s architectural marvels and bustling river activity. As you stroll, you’ll encounter four distinct districts, each with its own character and charm: the Confluence, the Arcade, the Civic, and the Esplanade.
The Riverwalk provides a diverse range of experiences. On Sundays, you can enjoy free concerts that fill the air with music. Relax in the comfortable Adirondack chairs positioned towards the east end of the path, perfect for soaking in the ambiance. Admire the captivating public art installations that dot the landscape. Indulge in inventive bites and refreshing cocktails at the various restaurants that line the Riverwalk, such as Beat Kitchen on the Riverwalk, Chicago Brewhouse, or City Winery at the Chicago Riverwalk.
As you explore, take in the picturesque views of boats and kayaks gracefully gliding along the river. Enjoy the vibrant people-watching opportunities, observing the diverse mix of locals and tourists. Throughout the year, the Riverwalk hosts seasonal events, such as the Riverwalk Fall Festival and Art on theMart, a mesmerizing display of large-scale projections on the facade of the Merchandise Mart. The Riverwalk is a true gem in the heart of Chicago, offering a delightful blend of recreation, entertainment, and cultural experiences.
12:00 PM: Wine Tasting at Verve Wine + Provisions
For a sophisticated and engaging wine experience, head to Verve Wine + Provisions, a trendy Lincoln Park destination that promises to expand your palate and deepen your appreciation for the world of wine. Here, you’ll find a staff of passionate and knowledgeable wine enthusiasts who are eager to guide you toward the perfect selection, tailored to your individual tastes and preferences.
Verve Wine + Provisions offers a delightful brunch experience on Sundays from 11:30 AM to 2:30 PM. Indulge in a delectable array of noshes and nibbles, ranging from fresh salads and fluffy pancakes to savory cheesy grits and hearty burgers. For a truly immersive experience, consider attending one of the celebrated tastings, where you’ll have the opportunity to sample a curated selection of wines and discover something new and exciting.
During these tastings, you’ll not only expand your knowledge of wine but also have the chance to purchase bottles to take home, allowing you to relive the adventure and share your newfound discoveries with friends and family. Verve Wine + Provisions is more than just a wine shop; it’s a destination that fosters a love for wine and creates lasting memories.
Day 1: Afternoon
2:00 PM: Immerse Yourself in The Office Experience
Fans of the beloved television show "The Office" will delight in exploring Chicago’s newest pop-up attraction, The Office Experience. This immersive adventure, located at The Shops at North Bridge on the Magnificent Mile, invites you to step into the world of Dunder Mifflin and relive your favorite moments from the show.
As you explore the exhibit, you’ll encounter iconic settings such as Schrute Farms, where you can immerse yourself in the quirky world of Dwight Schrute. Take photos in the meticulously recreated Dunder Mifflin office set, capturing the essence of the show’s workplace humor. Witness the unfolding romance between Jim and Pam in a dedicated set recreation that brings their love story to life. Marvel at the show’s costumes and props, gaining a behind-the-scenes glimpse into the making of "The Office."
Tickets for The Office Experience are timed and must be purchased in advance, ensuring a smooth and enjoyable visit. After your immersive journey, take some time to browse the shops at North Bridge for souvenirs and Chicago keepsakes, allowing you to commemorate your visit and bring a piece of the city home with you.
4:00 PM: Recharge at The Neighborhood Hotel
After a day of exploration, a well-deserved siesta is in order. Check into The Neighborhood Hotel, a stylish property located in the charming Lincoln Park neighborhood. Here, you can unwind, relax, and prepare for a fun-filled evening ahead.
The Neighborhood Hotel offers a range of accommodations, from one-bedroom to three-bedroom suites, catering to the needs of different group sizes. Each suite is equipped with a kitchen, allowing you to prepare snacks and meals at your convenience. Take a nap, catch up on your favorite television show, or simply relax and recharge in the comfortable surroundings.
What sets The Neighborhood Hotel apart is its location in a highly walkable neighborhood, encouraging exploration and discovery. Step outside and wander through the streets of Lincoln Park, immersing yourself in the local atmosphere and uncovering hidden gems.
Day 1: Evening
7:00 PM: Laugh the Night Away at The Second City
No visit to Chicago is complete without experiencing the city’s renowned improvisational comedy scene. The Second City, which first opened its doors in 1959, has been a breeding ground for comedic talent, launching the careers of legendary performers such as Bill Murray, Eugene Levy, Catherine O’Hara, Tina Fey, and Kate McKinnon.
Spend a few hours at one of The Second City’s evening shows and prepare to be entertained by hilarious improvisational skits, sketch comedy, and stand-up performances. The energy is infectious, and the laughter is guaranteed to be non-stop.
9:00 PM: A Culinary Journey at The Bristol
For an unforgettable dining experience, make a reservation at The Bristol, located in the vibrant Bucktown neighborhood. This acclaimed restaurant offers an exquisite eight-course tasting menu, paired with unique global wine selections.
As you progress through each course, you’ll embark on a culinary journey, gaining insights into the inspiration behind the chef’s creative dishes. From Hamachi tartare to heirloom tomato salad and yellow squash gazpacho, each plate is a work of art, designed to tantalize your taste buds and spark your curiosity.
11:00 PM: Skyline Views at Upstairs at the Gwen
What truly elevates a night out in Chicago is the opportunity to soak in the breathtaking skyline views. Head to Upstairs at the Gwen, an art deco-inspired rooftop bar that offers a sophisticated and intimate atmosphere.
This bright and colorful outdoor space is tucked away, providing a sense of privacy that sets it apart from other rooftop bars. Sip on inventive, Instagram-worthy cocktails while enjoying panoramic views of the city’s iconic architecture. Even when the weather turns chilly, the terrace remains open, with firepits and warming drinks and bites to keep you comfortable.
Other fantastic rooftop bars with dazzling skyline views include Cindy’s Rooftop, Chateau Carbide, and LH Rooftop. Each offers a unique ambiance and a memorable setting for enjoying the vibrant Chicago nightlife.
Day 2: Morning
10:00 AM: Explore The 606
Similar to New York City’s High Line, The 606, built on the former elevated Bloomingdale train line, offers a unique way to experience the urban outdoors. This once-abandoned rail line has been transformed into a multi-use park and public space, perfect for running, walking dogs, cycling, and picnicking.
Walk the entire 2.7-mile length, between Ashland and Ridgeway, or hop off at any one of the 12 access points. Keep an eye out for the public art installations along the way, including "A Greater Perspective," "Birds Watching," "Children Are Our Future," "Graffiti Garden," and "Turning Sky."
12:00 PM: Indulge in Deep-Dish Pizza
No trip to Chicago is complete without indulging in a slice of deep-dish pizza. Weigh in on the debate of which pizzeria serves up the best slice: Giordano’s, Lou Malnati’s, Pizzeria Uno, Gino’s East, or Home Run Inn? Each offers a unique take on this Chicago classic.
Day 2: Afternoon
2:00 PM: Chicago Architecture Foundation Tour
Chicago is renowned for its architecture, and one of the best ways to appreciate its iconic buildings is by taking either a guided walking tour or a Chicago River boat tour with the Chicago Architecture Foundation.
You’ll gain an in-depth understanding of Chicago’s history and the city’s most modern innovators. Be sure to see the Willis Tower, 875 North Michigan, Aon Center, Aqua, Tribune Tower, The Wrigley Building, Marina City, Civic Opera House, Merchandise Mart, and Chicago Water Tower.
Day 2: Evening
4:00 PM: Millennium Park and Maggie Daley Park
To beat the crowds, plan on visiting one of Chicago’s top tourist attractions, Millennium Park, in the early evening. Located next to the Art Institute, this celebrated public space is home to the Jay Pritzker Pavilion, Cloud Gate (aka The Bean), Crown Fountain, and Lurie Garden.
For those seeking adventure, Maggie Daley Park offers minigolf, a climbing wall, an ice-skating ribbon, and tennis courts.
8:00 PM: Japanese Cuisine at Roka Akor
Reserve a table at the much-talked-about Roka Akor for steak, seafood, and sushi. The Japanese wagyu is a celebrated menu item, as are any dishes cooked on the signature robata grill. Located on Clark Street in River North, you’ll have easy access to post-dinner nightlife.
11:00 PM: Explore River North’s Nightlife
After dinner, head out to a couple of Chicago’s noteworthy neighborhood bars. Popular bars in River North, all within walking distance of Roka Akor, include Hubbard Inn, The Boss Bar, and Arbella. Each locale offers a distinctive flair, providing a perfect ending to your 48 hours in Chicago.
